Matchmaker: A Cautionary Tale
by Virgo Writer
Summary: If there was one thing Ash Ketchum knew about . . . well it certainly wasn't matchmaking. And as well as the tried and tested clichés tended to work in movies, in real life, things tended to get a little . . . well . . . complicated. Pokeshipping.
1. The Plan

**Matchmaker**

Because the one thing you need from me right now is a NEW story. But this one'll be short and sweet and completed (in fact, it pretty much already is). I promise. It was originally intended to be one of my FF vs. RL drabbles, but I liked the idea too much not to make it a proper-ish story.

DISCLAIMER: I don't own **Pokemon**, but given my inconsistent writing habits, aren't you glad I don't.

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_Summary: _If there was one thing Ash Ketchum knew about . . . well it certainly wasn't matchmaking. And as well as the tried and tested clichés tended to work in movies, in real life, things tended to get a little . . . well . . . complicated. Pokeshipping w/ egoshipping on the side.

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Matchmaker: A Cautionary Tale

**_Step 0 - The Plan_**

"So are you going to tell me who you like?" Ash asked as he placed a basic energy card alongside one of his Pokémon cards. Gary looked at it disdainfully, scoffing at Ash's choice of attack.

"What makes you think I'm going to tell you?" Gary asked in reply, placing his own card dramatically down on the floor in front of him. The two sixteen year olds were sat on the floor playing a fiercely competitive game of Pokémon trading cards, and as usual, Ash was losing badly. The Sinnoh Champion, either in defiance or despite his exalted position, seemed to be incredibly bad at the game - a game that was intended to mirror an actual Pokémon battle strategy as closely as possible.

"Isn't that why we're playing this game?" Ash asked, playing another poorly chosen card against his active Pokémon.

Gary rolled his eyes. "How do you even know I like someone?" he asked suspiciously, narrowing his eyes at his friend. "Who told you?"

"How do you know I didn't work it out for myself?" Ash replied defensively. "The way you've been mooning around this last week, it was obvious to everyone." Gary gave him a sceptical look. "Okay, it was Daisy," he conceded.

"That loose-lipped cow," Gary muttered to himself and thought of all the ways he would be able to get back at his older sister.

"Dude, you can't talk about girls like that," Ash reprimanded. "Especially ones that are related to you. Even I know that.

"And even if Daisy hadn't mentioned it, I would have worked it out for myself eventually," he continued in defence of Gary's loudmouthed older sister. "I'm actually really observant when it comes to relationships and stuff."

Gary only meant to scoff very loudly at the comment, but he couldn't resist the loud and obnoxious laughter that followed Ash's declaration. Who wouldn't? This was the boy who still didn't realize that each and every one of his female (and one male) travelling companions had been hopelessly in love with him and didn't realize that most of the females (and some males) that had offered him aid or shelter had simply been trying to get into his pants. At least, that was how Gary viewed matters. That point was that Ash wasn't 'really observant' about anything, particularly 'relationships and stuff'.

"I am," Ash protested once Gary had finally stopped laughing. "I was the first one to notice that Tracy liked Misty," he said, hoping Gary wouldn't notice the way his features suddenly darkened with jealousy.

"Tracy liked Misty?" Gary asked, the sour note in Ash's voice going unnoticed as he tried to hide a similar tone in his own.

"Yeah," Ash confirmed. "While we were in the Orange Islands. He was always talking to her, and they'd have these sort of secret conversations, and he was interested in all the same stuff she was interested in, and he was always making weird comments about her looks like 'I wish I had your figure' and stuff. I'm surprised nobody else saw it."

"Me too," Gary replied drolly, seeing the truth in Ash's uncanny observations. "Who's he seeing now anyway?" he added in the hope of maybe making Ash see the light.

"Um . . . Danny form Navel I think," Ash replied. "You know, now that I think about it, he had a thing for Misty too – that pedo letch. What kind of guy scams on a thirteen year old girl?"

Gary just nodded, smiling tightly. _'I mean, who am I to set things straight – so to speak – for Ashy?'_ Gary justified to himself. _'Rock boy should have explained this stuff to him years ago.'_

"So, who do you like, Gary?" Ash asked, returning the conversation back to the topic that had begun it all.

"It doesn't matter," Gary waved off vaguely. "She likes someone else so it's not like I even have a chance with her."

"So you're giving up?" Ash questioned in surprise. "That doesn't sound like the Gary I know. Are you really gonna let yourself by bested by some chump loser?" he asked inspiringly.

"Not when it comes to Pokémon trading cards," Gary muttered under his breath as he finished the chump loser with a single card. "It's not like I haven't tried already," he said aloud. "You wouldn't believe the number of times I asked her out and she's seriously not interested."

"Well you're probably just going about it wrong," Ash assured him. "You can't just ask her out while she's hooked on this other guy. You've got to make her like you more than him."

Gary looked at him curiously, slamming his palm into his head a moment later for actually taking Ash's romantic advice seriously. "I can't believe I'm taking romantic advice from Ash Ketchum," he bemoaned loudly. "Remind me again what your credentials are, Ketchum? Who was your last girlfriend?"

"Well nobody," Ash replied sheepishly, blushing madly for no reason Gary could comprehend or cared to enquire after, "but I've got lots of girl friends," he added, emphasizing the disjunction between the two words. "I know loads about girls. I mean, I know Misty, and you don't really get more complicated than her when it comes to girls."

Gary nodded thoughtfully. Ash did make a good point about girls, and his close friendship with Misty put him in the prime position to offer advice. "Alright, Ketchum," Gary conceded. "What do you suggest?"

"Well . . ." Ash began thoughtfully, taking a moment to consider what was best. "I think what you should do is offer to help her get with this other guy . . ."

"What?" Gary exclaimed. "Are you serious? Why on earth would I help the girl I like get with another guy? It's ridiculous!"

"No, hear me out," Ash protested. "It works all the time in books and movies and stuff. See, the two of you will spend time together while you're scheming and because of that she'll develop feelings for you instead of the other chump. It's a guaranteed success. Misty's made me see a million movies like it with her and they all work out the same. The girl always ends up with the guy that tries to help her get the other guy. It's inevitable."

"Big word, Ketchum," Gary antagonized. "Do you even know what it means?"

"It means it's going to happen," Ash said surely.

"You so better be right, Ketchum," Gary warned. "Cos if it doesn't . . ."

"It's gonna work," Ash promised. "I guarantee it."

~ to be continued ~

Interesting start, right? I think there are two people you can take romantic advice from in Pokemon and just know it's going to end in disaster - one is Brock and Ash is the other. This story is short and sweet and almost complete in my writing of it, so it'll be weekly updates for this one. Let me know what you think.


	2. Put Into Practice

**Matchmaker**

I guess you all liked the first part well enough, so here is the next installment. Hope you enjoy.

DISCLAIMER: I don't own **Pokemon**.

* * *

_Summary: _If there was one thing Ash Ketchum knew about . . . well it certainly wasn't matchmaking. And as well as the tried and tested clichés tended to work in movies, in real life, things tended to get a little . . . well . . . complicated. Pokeshipping w/ egoshipping on the side.

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Matchmaker: A Cautionary Tale

**_Step 1 - Put Into Practice_**

Ash's plan was ridiculous. Gary knew it was ridiculous. But he didn't have a better plan so he thought, 'what the hey? Let's see if it works'. If it did, it did. And if it didn't, then it wasn't like he'd really lost anything. He'd simply be right where he started – no better or worse – only this time he could blame it all on Ash. That, he considered, was a win-win situation.

And so, with Ash's plan only vaguely outlined in his head – after all, he couldn't give Ash the necessary details for cementing the plan without giving himself away – he made his way to Cerulean City to make a fresh appeal for the current love of his life. He was met at the front door by Misty's eldest sister, who – as always – greeted him with a flirtatious smile that he knew better than to give serious thought to. He knew far too many guys who had been burnt by Daisy Waterflower to believe that a flirtatious grin from her meant anything more than extreme friendliness.

Of course, that didn't stop him from flirting a little back. "And how are you today, Miss Daisy?" he asked dapperly. "You look lovely, but that's not all that unusual for someone as naturally lovely as you."

"Charming as always, Gary," Daisy grinned back, a gay laugh lilting the air. "I suppose you're like here for your bi-weekly rejection?" she asked him with amusement lighting her blue-green eyes.

"What can I say?" Gary shrugged, a lazy grin on his lips. "I'm determined to succeed."

Daisy scoffed in a surprisingly adorable way. "I'd say you're a masochist, Gary Oak," she told him. "I think you almost enjoy it," she added with a seductive wink before turning suddenly teasing. "Unless you're like really here to see me and this business of asking out my baby sister is just like a cover."

She chortled at the thought, turning away from him momentarily to make a loud cry out towards the back reaches of the gym. "Misty, you've got like a gentleman caller!"

"Yeah, I noticed," Misty replied dryly. She entered the room immediately after Daisy's cry, tying up her hair on the top of her head as she walked.

"Does this mean you've started to anticipate my visits, Red?" Gary asked with a smile as he drifted away from Daisy and towards the current object of his affections. He turned his charm up to its highest level, knowing anything short of maximum charm would be completely ineffective on Misty.

Misty sneered at him, the nickname alone making her practically gnash her teeth. "It means I've come to associate the sudden cloud of smog and the waft of cheap cologne as indicators of your presence," she told him snarkily and crossed her arms tightly over her chest. "Don't think for a second I'm happy to see you."

Gary looked unaffected by her harsh words. "You say that now . . ."

"And I'll keep saying it until you get the hint," she finished for him, scowling to prove her point. "Can we just get this over and done with so I can go back to my training? I think I've almost made a breakthrough with Psyduck's swimming lessons and Gyarados is in desperate – deserving – need of my attention."

"I guess," Gary conceded reluctantly, Misty's impatience somewhat disheartening. "I actually came today to offer you my services," he said, doing his best impression of shyness.

"Well that's a new one," Misty muttered sarcastically, rolling her eyes. "In case it wasn't obvious the million times before now, I have no need, desire, or interest in any services you have to offer," she told him pointedly, a sharp gesture of her hand emphasising each word and her lip curling in disdain as she spoke.

"You didn't even hear what they are," Gary protested weakly.

"Oh c'mon, Misty. Just give him a chance," Daisy encouraged. "Go on, Gary," she suggested before Misty could interject and disparage him further.

"Right," Gary began awkwardly. He had forgotten that Daisy was still there as he tried to convince Misty of his good intentions with all the subtlety of an antelope at a hunting convention. "I wanted to . . . uh, help you . . . with Ash."

"What about Ash?" Misty replied with a glare. Her voice dropped dangerously low and her jaw clenched. She was clearly still in the denial phase.

Gary rolled his eyes. "Let's just pretend for a second that you liking Ash isn't the worst kept secret in all of Kanto," he replied sarcastically. "Ash and I are friends, and I've known him longer than you and Brock combined, so I'm in the prime position for helping you win Ash's heart."

"I'm not . . . he isn't . . . and a-and I . . ." she spluttered adamantly, her flushing cheeks defeating any argument she was trying to make. "I have no interest in Ash's heart," she said snootily as soon as she found the words, the threatening look in her eyes just daring him to say otherwise.

"Except you totally do," Daisy answered unhelpfully on Gary's behalf. "And Gary is being totally helpful so like stop being such a bitch, baby sister, and just accept help when it's offered to you."

Misty gaped at her sister, unable to believe that Daisy was being so forthright and taking Gary's side. "Fine, whatever," she muttered with a wave of her hand. "Do what you want."

Gary beamed, phase one of his plan (well . . . Ash's plan) a complete success (relatively). "You won't regret this, Misty," he assured.

"I will," Misty muttered darkly in reply. "I can almost guarantee it."

Gary tensed. He felt a strange need to back away slowly when that tone reared in Misty's voice, and he could tell that Daisy was having similar thoughts as she made desperate glances towards the three exits in the room. She almost jumped out of her own skin as a figure appeared suddenly in one of the exits, carrying two fishing rods (one full sized and one miniature) over his shoulder.

"Hey, Myst! Do you wanna go fishin'?" asked a loud and naturally boisterous Ash as he walked into the room with his prized Pokémon, having made his way into the gym without any of the polite pretence Gary had used to gain admittance. He grinned at his best friend, waving the fishing rods at her invitingly and remaining completely oblivious to the tension in the room . . . or the way it seemed to spike with his sudden presence.

"Oh hey, Gary. What are you doing here?" he asked as he noticed he other occupants in the room. He offered Daisy a polite wave, but for the most part ignored her without the slightest guilt.

"Just running an errand for gramps," Gary lied.

Ash nodded without giving it any further thought. If he had, he'd wonder what sort of errands Professor Oak could possibly have in Cerulean two days running, as Tracy had been sent on some business just yesterday morning. Instead he turned his attention back to his best friend, thinking of no one but her and her answer to his question. "So what do you say, Myst? I think I know a rock with your name on it."

Misty laughed happily at his goofball reply and untied her hair in a way that she hoped looked completely casual. She moved closer to Ash, her posture seeming to relax with his presence and a smile spreading across her previously grim features. "Like I need any more encouragement than that," she teased affably. Her whole mood seemed to do a complete turn around from dark and irritated with Gary to bright and happy with Ash.

"But, Misty, what about ps – " Gary began, trying to remind her of her duties to her Pokémon training that she had cited earlier in order to get rid of him. He was, however, stopped from doing so by a subtle kick to the shin from Misty.

"I'll just go get my stuff," Misty said. "Are we going to the usual spot? Or were you trying to catch something in particular?"

"Not really," Ash shrugged and followed her as she made her way out of the room. "Can't a guy just want to spend some quality time with his best friend?" he asked, nudging his shoulder into hers. "Well, best human friend," he added with a gesture towards Pikachu, who lagged slightly behind the pair in his proper fishing attire.

"Maybe, but I still suspect a motive," she replied with a laugh.

Gary's eyes widened in near panic as he watched Ash Ketchum flirt with HIS current love interest. He had to work to keep his expression neutral on seeing this, his only consolation being that Ash wasn't particularly good at flirting (a rock with her name on it – puh-leez) and that Misty was wilfully blind to the meaning behind Ash's actions and words. But no matter how bad Ash was with regards to the opposite sex, Gary was quite certain of what he was seeing and he knew he had to put a stop to it before it went too far.

"Hey, guys, do you mind if I come with you?" he asked suddenly, halting them in their path. They turned simultaneously, both giving him meaningful looks that seemed to say the exact same thing: TAKE IT BACK!

Ash's gaze shifted suspiciously as he desperately searched their surroundings for some kind of out. "I . . . uh . . . I don't have another fishing rod," Ash tried awkwardly, knowing immediately that it was a terrible excuse. They were, after all, in a Water Pokémon gym and the Waterflower sisters (Misty in particular) owned almost as many fishing rods as there were water-type Pokemon. "I guess Misty could lend you one," he added lamely, "so I guess if it's alright with her . . ." he said, hoping it wouldn't be.

"Well, if it's alright with you . . ." Misty responded with equal awkwardness, her words conveying to anyone just slightly less dense than Ash that it was not alright with her in the slightest. She glared at Gary, trying to mouth instructions to him of exactly what his response should be – something along the lines of 'you know what, I think I have another engagement so maybe another time' – while Ash wasn't looking.

"Cool," Gary said, ignoring both Misty's silent instructions and the various non-verbal cues from the two of them that said his presence was _not_ wanted.

"I'll just get you a fishing rod," Misty replied tightly, her words seeming to imply a desire to impale him with said rod. She turned on her heel, taking Ash with her as she want to get what was needed. As before, they made subtle, intimate touches along the way – Gary, for the most part, already forgotten.

"Gary," Daisy started once she was sure they were far enough away, "you like better be serious about helping Misty, 'cos like if this is just some ploy to get her, it's not going to work. You're like not going to win. Not against Ash."

"Seriously, Dais'?" Gary replied casually with a half-laughing smirk on his face. "What do you think this is? Do you think I got romantic advice from Ash Ketchum telling me I should pretend to help her get with the guy she likes so that she'll fall in love with me in the process? That I'd go and base my whole premise for wooing her on a clichéd romantic-comedy plot that just barely works in movies? That's ridiculous, Dais'."

"You're right, that sounds totally ridiculous," Daisy giggled. "Like, what was I thinking? I think I've seen like too of those movies for my own good.

"I guess if you're with them now, you can like help them see that their feelings are totally mutual," she said, convincing herself of the plan even as Gary came up with his own, more devious version of how things would progress.

"Totally mutual," Gary muttered in agreement. He wondered how he'd managed to miss the fact that Misty's unrequited loved for Ash Ketchum wasn't quite so unrequited, especially given that even Daisy could see the truth. It was kinda obvious now that he realized it, because even though Ash never seemed to show any interest in his female travelling companions, he'd always had a special place for Misty Waterflower that seemed to go well beyond the realms of friendship.

Not that such a thing would stop Gary from trying his darndest to steal Misty right from under Ash's nose. As far as Gary was concerned, Ash had had his chance – he'd had six years of chances – and now it was Gary's turn.

And nothing was going to stop him from getting what he wanted.

~ to be continued ~

Uggh, I didn't want to write an evil Gary, but this story just went and took its own course. It was supposed to be slapstick humour, but somehow managed to gain a dramatic tone that I hadn't intended from the first chapter. And Gary's not entirely evil, just a little self-absorbed and not a particularly good friend, so he's only mildly OOC (at least with post-Johto Gary who was kinda OOC of the original series Gary - I can actually see the old Gary doing exactly this sort of thing).

So now that Ash's got some serious competition to contend with, will he finally step up to the plate and make a play for Misty's heart? Will Gary somehow prevent Ash from throwing his hat in the ring? Or will Misty's succumb to Gary's ingenious plan to distract her from her feelings for Ash?

Find out in the next stage of Matchmaker: A Cautionary Tale and in the meantime, review!


	3. Revision

**Matchmaker**

And now, for your supreme enjoyment . . . more Evil-Gary!

DISCLAIMER: I don't own **Pokemon**.

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_Summary: _If there was one thing Ash Ketchum knew about . . . well it certainly wasn't matchmaking. And as well as the tried and tested clichés tended to work in movies, in real life, things tended to get a little . . . well . . . complicated. Pokeshipping w/ egoshipping on the side.

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Matchmaker: A Cautionary Tale

**_Step 2 - Revision_**

"She's not interested," Gary said in a low voice, lagging behind with Ash as Misty and Pikachu led the way to some new fishing spot near Cerulean Cove. Apparently their 'usual spot' was some sort of secret that couldn't go beyond the charmed circle (one that consisted of Ash, Misty, and their Pokémon), and Misty had made up some excuse about a great new spot near by simply to avoid extending that knowledge to Gary.

"Huh?" Ash asked, feigning ignorance. Or maybe not. Maybe he really, truly, honestly had no clue what Gary was talking about and wasn't playing dumb like Gary suspected. Gary couldn't really be sure either way, but continued on the assumption that he was only feigning ignorance.

"Misty. She's not interested," Gary said again, keeping his voice to a low hiss. He noted Pikachu's quirk his ears back in their direction at the sound of Misty's name and realized he was going to have to be careful if he didn't want the little rodent going around ruining his plans.

"Not interested in what?" Ash asked, frowning in confusion as he tried his best to decipher what exactly Gary was trying to say. "Do you mean she didn't really want to go fishing with me?" Ash asked, looking suddenly inconsolable. For a moment, Gary almost felt bad for what he was trying to do, but once again reassured himself that if Ash hadn't been such a coward for the last six years, none of this would be happening, ipso facto, it was all Ash's fault.

Gary rolled his eyes, coming to the easy conclusion that Ash Ketchum wasn't _playing_ dumb. "You, you moron," he hissed in reply. "She's not interested in you."

It took Ash a few moments to realize what exactly Gary was getting at, and when he did, his expression dropped entirely. Gary didn't think he'd ever seen the Sinnoh Champion looking so forlorn in his life, not even when his dad left or when they stopped being friends. He had probably just broken Ash's heart, and the full extent of that was written all over his face.

"Do you think she knows?" Ash asked quietly, his voice barely rising to a whisper. He glanced down at his feet, lowering the brim of his hat so it would shadow his face and hide his broken expression.

"I don't know," Gary shrugged. "I don't think so.

"You'd hope not," he added empathetically. "It would just be so _uncomfortable_ for her if she did. Imagine how awful it would be for her after so many years of friendship to find out that you felt _like that_ about her. It would be so awkward. Christ, it might even ruin your friendship and I know how much Misty treasures what the two of you have."

"Yeah," Ash agreed painfully. "I couldn't do that to her. Not to Misty."

"Hey, it's okay, Ash," Gary said consolingly, patting his childhood friend on the shoulder. "It's not like you've done anything wrong. It's not your fault you fell for her. Misty's a great gal – christ, I bet she has guys falling for her all the time. You're probably just one of the many millions to fall prey to the Waterflower charm."

Ash was torn between being impressed or simply aggravated by Gary's skill with words. Every phrase was like a precisely aimed projectile, tearing another sliver off his wounded heart. His strong friendship with Misty, which had withstood distance and time and all kinds of obstacles and adversity, was suddenly in jeopardy all because he had the _audacity_ to go and fall in love with her – through no fault of Misty's – just like the millions of other guys around her.

He sighed, his breath shaking with the heavy emotions he tried to expel. "Just because she doesn't . . . I . . ." he began, trailing off with the meaning implicit. "You've got to help me, Gary," he said, turning to his childhood friend. "She can't know. It would ruin everything."

Gary nodded gravely, resisting the smirk of victory that pulled at his lips. "There's only one thing to do," he insisted in a pensive tone. "You've got to convince her that you like someone else. That way if she ever suspects anything, it'll throw her off the scent."

"Gary, I'm not sure – "

"C'mon, Ash, I know what I'm talking about," Gary encouraged, cutting off Ash's protests. "It's for the best."

Ash made to give further protest, but made the mistake of looking in Misty's direction. She looked so happy and carefree, and he knew that would change if she ever found out how he really felt about her. She was the love of his life, and above all else, he wanted her to be happy.

He sighed in defeat, giving in to Gary's plan. "What do I do?" he asked sadly, his body slumping sadly.

"Just follow my lead," Gary answered, raising his voice subtly a moment later so Misty could finally hear them. "Wow, Ash. She sure sounds like something special," he said conversationally, watching as Misty's steps faltered for just a second.

"What are you guys talking about back there?" Misty asked nonchalantly over her shoulder. She barely glanced in their direction (well, Ash's) and pretended as though she only had a vague interest in their goings on that had absolutely nothing to do with the sudden use of a feminine pronoun.

Ash's face contorted into surprise and horror, his expression playing perfectly into Gary's plan. Gary turned his own features to a half-sheepish, half-apologetic smile. "Nothing," he said quickly – _'a little too quickly_', Misty thought, taking this as overwhelming evidence that they were in fact talking about something. "Just guy stuff," Gary added with a cheesy smile.

Misty looked upset by her exclusion from the conversation, but pushed past it quickly. "Well, the spot is just around this corner," she said, changing the subject. "It's really nice."

Ash scoffed a little, knowing full well that the fishing spot they were heading towards was okay if you were in the market for shellder or horsea or the miscellaneous junk that seemed to come up a lot in this spot, but nothing particularly special. But then again, like Misty, he wasn't particularly keen on the idea of letting Gary in on _their_ fishing spot unless they really had to, so he was happy to go along with the ruse.

Gary grinned, watching the pawns in his clever plan move into place. "Don't worry, Ash," he said lowly, "now you've got me on your side, I'll make sure that Misty never knows.

"You can trust me, Ash," he added with an almost sinister grin. "I won't tell a soul."

* * *

Misty felt a hard tug on her line and turned to Ash challengingly. "Right boot," she gambled as she held her line steady.

"Tossed PokéDoll," Ash replied.

"Pik pika chu," the mouse-like Pokémon suggested, putting his own bet in.

"Brave," Ash noted with an amused look, "but highly unlikely, Pik."

"Loser has to go find some more bait," Misty reminded them as she started reeling in her catch. Whatever was on the end of her line resisted, but with one hard tug, she eventually pulled it free, flinging an old brown boot onto the river bank.

"Yes," Misty cheered, throwing the boot next to its forgotten mate. "I am so good at this game."

"You two are weird," Gary complained, watching the pair with a scowl. "We've caught nothing but crap all day," he said and gestured towards the pile of random items they had fished out, "and you're both acting like that's a good thing."

They both shrugged, neither one of them pointing out the fact that Gary had no business complaining given that no one had actually invited him to come along.

"C'mon, Pik," Ash said, picking up the metal bucket. "Let's go find ourselves some grubs." With a 'chu' of agreement, the two disappeared back into the woods around them.

"So what were you guys talking about earlier?" Misty asked quickly as soon as Ash was out of hearing range. "It looked pretty serious."

Gary forced his expression into a grimace, looking at Misty reluctantly. He had known this moment would come just as soon as Misty had reason to get Ash out of the picture, and he was honestly surprised that Misty had lasted as long as she did. The Waterflower women weren't exactly known for their patience, and Misty even less.

"Misty, I don't think I should say," he told her. "Ash is my friend and what he told me was in strict confidence. I don't think I should be breaking his trust like that. If he wanted you to know, he would have told you."

Misty narrowed her eyes – she didn't buy Gary's contrite act, not even for a second. "The only reason you're here right now, Oak, is because you said you'd help me with Ash," she told him darkly, "so either start talking or start finding your own way back to the gym. Capisci?"

Gary nodded. He choose his words carefully, pausing intermittently to give the impression of an unwillingness to part with the information. "He . . . uh . . . was telling me about . . . about a girl he likes."

"He . . ." Misty began, her breath shaky as she tried to form the words. "He likes someone else?"

"Yeah," Gary admitted with a pained smile. As with Ash, Misty's face dropped with that single word and tears were evident in the corners of her eyes. "But it's nothing to worry about," he added consolingly. "She's completely out of his league and he doesn't have –"

Misty grabbed him roughly by the collar, cutting off anything else that Gary had to say about the matter. "What do you mean she's too good for him," she growled. "What the hell is wrong with her? Is she blind, or just really, really stupid?

"Who is she?" she asked angrily. "Tell me and I'll show that little tart who she's better than. Ungrateful cow. Doesn't she know how lucky she is?"

"It's fine, Misty," Gary said, trying to calm her down and wrench himself out of her grasp at the same time. He definitely hadn't been expecting this reaction from Misty. She was supposed to be inconsolable and falling into his arms, maybe even a little jealous. She wasn't supposed to be up in arms defending Ash's honour against some girl that didn't even exist. It seemed he had somewhat misjudge the situation.

"I don't know who she is exactly, but that's what Ash said: 'she's out of my league'," he tried and attempted to appease her, "and for our purposes it's good that he feels that way. She doesn't actually matter in the scheme of things."

"How do you know?" Misty replied. She let him go, but only so that she could take on an intimidating stance with her hands poised in her hips and her shoulders squared. "He might really, really like this girl and we're just –"

"He doesn't," Gary cut in. "It's just a crush. Nothing serious. Believe me, Misty, the girl doesn't matter.

"Just forget about the girl," he insisted, "because I have a plan for how to get Ash. I mean, obviously Ashy-boy isn't quite as disinterested in girls as we once thought, so we've just got to get him thinking about you in the right frame of mind. And to do that, all we've got to do is make him jealous."

Misty rolled her eyes. "And how exactly do you propose we do that?" she asked with a sneer of disbelief.

Gary grinned. "By going out on a date with me, of course."

~ to be continued ~

And now Evil-Gary's sinister plans begin to take form. You can all see why a regular old Gary just wouldn't have worked here right, and at least he does show some signs of guilt through his single-mindedness.

Just two chapters left of Matchmaker: A Cautionary Tale. Reviews will not increase the speed of update - they never do - but it will make me happy and you do want me to be happy, right?


	4. A Date with Destiny

**Matchmaker**

Final chapter! Well, sort of. The real last chapter is short and doesn't really count because it's more for the sake of completeness, and thus will follow this more closely than usual - expect it Friday, or Thursday depending upon your timezone.

DISCLAIMER: I don't own **Pokemon**.

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_Summary: _If there was one thing Ash Ketchum knew about . . . well it certainly wasn't matchmaking. And as well as the tried and tested clichés tended to work in movies, in real life, things tended to get a little . . . well . . . complicated. Pokeshipping w/ egoshipping on the side.

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Matchmaker: A Cautionary Tale

**_Step 3 - A Date with Destiny_**

"I don't understand," Ash complained, scratching his head in confusion. "How . . . how did you get Misty to even agree to somethin' like this?"

"It doesn't matter," Gary agreed quickly, mostly because it did.

"I suppose not," Ash shrugged, acquiescing sooner than he should have. "I guess . . . I mean, it's just not . . ." he trailed off, struggling to find the right words but eventually just giving up and coming straight out with it. "I just . . . didn't think Misty liked you very much," he admitted sheepishly.

Gary glared in response. "Well let's just say I can be pretty convincing when I want to be," he answered vaguely and when Ash still didn't look convinced added the more believable, "Misty's sisters helped."

"Okay," Ash nodded. "You didn't tell them, did you?" Ash asked, looking suddenly panicked.

"Of course not," Gary assured him, because that would completely ruin his plans. "I promised I wouldn't tell anyone, didn't I?"

"Yeah," Ash said nodding his head. He fidgeted as they waited, absentmindedly adjusting and readjusting his tie, and running his fingers through previously tamed raven locks.

"You're not backing out, are you?" Gary asked through narrowed eyes. Something about the way the younger boy was standing seemed to suggest that he was likely to flee at any moment.

"No, I just . . ." Ash began, still looking rather antsy. "I was talking to Brock, and he said maybe the reason Misty's not interested is 'cos she thinks I'm not interested and that maybe I should tell her how I feel and . . . well . . . you know," he explained with a shrug and a hopeful look. "Things will work out."

Ash's sudden doubt aggravated him, but Gary did his best not to let it show. "I suppose that's one way of looking at it," he said, "but who are you really gonna believe here, Ash?"

"It's just . . . me, Brock, and Myst . . . we've been best friends since I started my journey, and I guess if anyone might know what Misty's thinking it'd be Brock, right?" Ash suggested, looking guilty for suddenly doubting Gary who was helping him out of the goodness of his heart.

"And what am I? Chopped liver?" Gary asked, half-joking/half-scathing in reply. "Rock-boy might know about Misty" – although Gary thought this was highly doubtful – "but I know about women. Unlike Brock, I know when a girl is or isn't interested, and believe me when I say, Misty just isn't interested and you'll only ruin things if you try to force her to return your feelings."

Gary was lucky that there weren't more voices opposing his appraisal of Misty's feelings for Ash. He was lucky that his version was all the more convincing than Brock's simply because the consequences of Brock being wrong were so devastating Ash could barely start to consider the benefits of him being right. He was lucky that Ash had spoken to Brock and not to someone who's compelling words weren't quite so easily refuted with evidence of near constant failure with the opposite sex.

He was lucky that their 'dates' arrived before Ash had the opportunity for further introspection.

"Well don't you clean up good," Misty teased as she spotted them, paying particular attention to her best friend. She made a near useless attempt at trying to tidy his messy locks once again and he responded by playfully swatting at her hands, which made her smile despite the feelings of impending doom this evening seemed to instil in her.

"You look really nice," he told her sincerely with a crocked half-smile, his hand twitching at his side as it longed to take its usual nervous position at the back of his head.

"Um . . . you too . . . uh . . ." he added quickly, turning his attention to the purple-haired girl beside his best friend. He knew he should know her name, but nothing came to mind. There was something vaguely familiar about her that made Ash frown in consideration.

"You remember Casey, right Ash?" Misty asked with a sweet smile.

"Yeah, of course," Ash agreed, obviously lying to save face. "It's good to see you again, Casey. How've you been since . . . Johto?" he guessed.

Casey shook her head and turned to Misty with a bright laugh. "He has absolutely no idea who I am, does he?" Casey asked.

"None what-so-ever," Misty agreed, "although I do think that was a very nice touch there with the region," she commented to Ash, "and a very lucky guess."

"Shall I remind him?" Casey grinned wickedly.

"Don't you dare, Casey," Misty warned. "If I have to hear the Electabuzz song one more time I swear I will kill. The only thing more annoying than that stupid song is the Team Rocket motto."

"Wait, I remember you," Ash said, the mention of electabuzz sparking his memory to life. "I thought you were a boy."

"Ash," Misty gaped, "that's really rude," she admonished. "How can you even make that mistake? 'Casey' is a girls name."

"So's '_Tracey_'," Ash shrugged in reply.

Misty rolled her eyes and took on a more rigid stance. She was readying herself for a verbal battle with Ash, and its commencement was only forborne by Gary's sudden interjection.

"Why, Misty, you look incredibly lovely tonight," he said smoothly, taking Misty's hand and brining it to his lips. "You're like a bright, blazing firework lighting up the room in all her glory."

Ash's fists clenched at his side as he tried to fight the jealous response that threatened to bubble out of him. Misty bit hard on inside of her cheek in order to prevent her expression turning into a grimace of disgust. Casey, who had no need to feign some other response, simply rolled her eyes at Gary's cheesiness.

"Why don't we go find our table?" Casey suggested to the group before turning to Misty in a quick aside, "If we let him talk any longer, I think I'm going to end up retching my dinner before I eat it."

"Me too," Misty whispered in agreement. "I think whatever woman deluded him into thinking he was charming should be severely punished for the consequences," she added humorously.

Gary, oblivious to the comments between Misty and Casey, pulled out her chair for her once they reached their table, indicating to Ash that he was to do the same for Casey. Casey, however, waved Ash off before he got the chance to attempt chivalry, letting him know that she was perfectly capable of seating herself.

"Good," Ash smiled, relaxing a little with the knowledge that he wouldn't be expected to play too far outside of his normal self to get through the evening. "So what have you been doing these last years?" he asked. "Have you done much travelling?" He was genuinely curious – as he was about all his past acquaintances – but he was also following Gary's instructions. He was to pay careful attention to his date for the entire evening so that Misty would not suspect where his heart truly lay.

Casey, unsure of what her role was supposed to be, was happy to oblige. She took the opportunity to enlighten Ash to the complicated politics and goings on of the Electabuzz team over the last year and how this had impacted upon their performance in the various league competitions, and Ash suddenly remembered why he couldn't _stand_ baseball.

"C'mon," Gary hissed at Misty who was seated beside him, "it's time to put the plan into action."

Misty rolled her eyes. "Forget it," Misty replied in a harsh whisper, "the plan is stupid and I'd rather poke my own eyeballs out with blunt utensils than pretend to enjoy your company."

"But the plan . . ." Gary tried whiningly.

"Is no longer in operation," Misty hissed back. "Hey, Casey," she cut into the conversation across from her, deciding to take pity upon Ash, "why don't you tell Ash about Meganium?"

Casey did so with great enthusiasm and Ash mouthed a silent 'thank you' towards Misty while the purple-haired girl wasn't looking.

Gary stewed. The plan wasn't going anything like he planned. Ash wasn't showing anything but his usual friendliness towards Casey. Misty was neither jealous nor depressed by Ash's lack of attention towards her, in fact, she even seemed to be joining in on the conversation. No one was paying attention to him, particularly not Misty, and so nothing was being done to further cement Ash's impression that Misty was out of his league (which Gary totally thought she was). His carefully placed pieces were all moving on their own accord and nothing was happening the way it was supposed to.

And Gary simply couldn't have _that_. Not when he'd put so much time and energy into getting things into place.

"Misty, can I talk to you for a moment?" he said charmingly, drawing her from the conversation for a moment.

Misty rolled her eyes. "What is it now, Gary?" she complained.

"I've got something I need to tell you," he said seriously, glancing over at Ash in the hope that younger man might make the wrong assumption. "It . . . could change your whole view on things."

Ash's face froze and Gary smiled to himself as Misty reluctantly left her seat.

"You were saying, Gary?" she asked pointedly once they found themselves a secluded alcove.

"Hey, don't give me that look," Gary protested. "I'm just following the plan," he said before muttering, "unlike some people."

"And I told you we were ditching the plan," she answered dangerously. "You said you'd help me, Gary, and like a fool I let you. As far as I can tell, you're not helping at all. You're just being your usual smarmy self and that's it. I should have known better – I should have known that a jerk like you will always be a jerk."

"I'm helping plenty," Gary replied. "Didn't you see Ash's face?"

"Yes," Misty replied, "because you're obviously holding something over Ash's head that got him to come here tonight. I can't believe even you would sink that low, Gary," she told him angrily. "Ash is your friend and you're pretty much blackmailing him right now, for what? For a fake date with a girl that can't even stand the sight of you? So you can covertly convince me that I'm wasting my time pining over Ash when I could have a guy like you?

"Why on earth would I choose someone like you over Ash?" she asked him with a cruel laugh. "He's kind and honest and would never try to manipulate the situation like this. And what are you? Some slobbering jerk who would do just about anything for his own gain."

At that Gary broke, taking a step forward that forced Misty up against the wall. "You're deluding yourself, Misty," he hissed at her. "Ashy-boy ain't nearly as perfect as you think. Not even by a long shot. Because you know that perfect, kind, honest guy you seem to think you know so well – he's the one that told me to do it. It was his idea.

"All of this," he said, waving his hand around grandly, "comes courtesy of Ash Ketchum.

"So, how do you like him now, Misty?" he asked cruelly. "How do you like it now that Ash Ketchum is 'someone like me'? Do you still want him? Do you think you could be friends with someone like that? Someone who deceived you? Someone who-"

"Stop," a voice called out, stopping Gary from going further. Gary jumped back in surprise and glanced in the direction of the interjector. "She gets it," Ash said despairingly, his body slumping in defeat as Gary – he assumed – revealed his worst secret, "you don't need to keep rubbing it in.

"Misty, I'm sorry," he said, turning to his best friend. "I'm sorry I ruined everything. I just . . . I'm so sorry, Myst."

Misty stared at him, her mouth agape in shock as she comprehended what Gary had just revealed and Ash's seeming confirmation of that. "Ash, how could you?" she asked sadly, tears sliding freely from her eyes.

"How could I not?" he replied, giving her a look of wonder. "You're impossible not to love, Misty," he told her with a beautiful half-smile.

"I don't understand," she complained, shaking her head and not quite believing his words. They simply weren't matching up with what Gary had just told her, and as loathe as she was to believe Gary, she couldn't entirely disregard them. It was just like Ash to go and do something like this, and then confess his undying love a moment later.

"Is that why you did it?" she asked him. "Is that why you helped Gary manipulate me? Because you love me?"

"Yes," Ash agreed eagerly, not fully attending to her stream of questions. He took it back once he considered them as a whole. "No, wait. What do you think I did?"

Misty shook her head and released an exasperated sigh. "Did you get Gary to bring me to dinner tonight?" she asked.

"Yes," he said with a nod, "but I didn't ask him to hit on you," he added with a glare directed at Gary. "He was only supposed to help me show you that I wasn't interested."

"Why?" she asked him cautiously.

"To avoid all this," Ash replied with a sad shrug. "I'm so sorry, Misty. I never meant to ruin our friendship like this."

"Why would it ruin our friendship?" she asked him, taking a cautious step towards him.

"Because now things will be all awkward and uncomfortable," he answered, practically reciting from Gary's warnings. "Don't worry, Myst, I don't expect you to return my feelings and I know you don't feel that way and that's okay because you're still my best friend and I'll always think of you that way and . . . um. I guess I should go," he said with a sigh, "I don't want to make this any weirder for you than it already is.

"I mean, I get that you're not interested so don't think that I'm trying to put any pressure on you or anything . . ." he said trailing off awkwardly.

"Not interested?" she couldn't help but ask.

Ash sighed in aggravation. "You know," he began to explain in the most basic of terms, "not interested in like . . . a relationship. Except friendship, but obviously that's out of the question because now you know and it'd just be too weird for us to stay friends after what I did."

Misty shook her head once again, unsure of whether she should be laughing or crying after Ash's botched confession. "Don't I get a say in this?" she asked him, her lips quirking at the corners.

"Well, I guess if you want to be friends, then of course that's okay with me, Myst," he told her, an eager hope lighting his eyes.

"And what if I don't?" she asked and his expression shifted once again to desolation as he looked down at his feet. "What if I want more?" she added, quirking her head to the side expectantly.

His head lifted, his eyes rising to meet hers. They were filled with a myriad of confused emotions, but there was hope and love and timid happiness that prayed her last question meant what he thought it meant.

"I don't know who's been telling you otherwise, Ketchum," she began with a laugh, "but I am most definitely interested in a relationship with you. In fact," she added casually, "I'm kinda in love with you too."

"You – you?" Ash questioned, struggling to find the words. He inched closer as his body moved entirely on its own accord.

"Yeah," she replied shyly, glancing coyly at her feet. "I thought it was obvious."

Ash shook his head adamantly, his steps bringing him determinedly closer to her. "Not obvious," he assured her. "At least, not to me."

"Well, now you know," she shrugged, closing the remaining space between them with a step forward that had their bodies pressed close together, "so what are you going to do about it, Ketchum?" she challenged.

Ash grinned. "What I've wanted to do for a really long time," he told her breathlessly. And with those final words of warning, he took her face in his hands and succinctly guided her lips to his own in a soul-searing kiss.

"I love you," he breathed gently against her lips as they parted for air.

Misty grinned. "I love you too."

~ to be continued ~

Ah-ha! Evil-Gary is defeated by his own evil ways. That'll teach him for trying to get between Pokeshipping - no one messes with my OTP and gets away with it, which is thusly what the last little chapter type bit consists of . . . REVENGE!

In the meantime, review.


	5. The Equal and Opposite Reaction

**Matchmaker**

And here it is - the end. Thanks everyone for reviews, favourites, and alerts and I promise I'll be updating one of my multichapter-epics next week.

DISCLAIMER: I don't own **Pokemon**.

* * *

_Summary: _If there was one thing Ash Ketchum knew about . . . well it certainly wasn't matchmaking. And as well as the tried and tested clichés tended to work in movies, in real life, things tended to get a little . . . well . . . complicated. Pokeshipping w/ egoshipping on the side.

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Matchmaker: A Cautionary Tale

**_Step 4 - The Equal and Opposite Reaction_**

"So what do you think we should do with him?" Misty asked, crossing her arms over her chest as she stood threateningly before the (for a lack of a better word) accused.

Ash sucked a breath in with a loud hiss. "I don't know, Misty," he said. "Don't you think this is punishment enough?" he asked and then demonstrated exactly what the punishment was by pulling her into a very _un_-chaste kiss.

"You make a good point," Misty nodded. "This," she said, pulling him back for another kiss and then pulling away, "is certainly a desirable punishment."

"And fun to carry out," Ash grinned at her, looping his arms lazily around her waist.

"I think I'm going to be sick," Gary complained from his prone position, restrained in a kitchen chair. "What about Ash?" he argued desperately. "How come he doesn't get punished when it was his idea?"

"Oh believe me, he will be," Misty answered and winked in Ash's direction. Ash shuddered in anticipation.

"You know what?" Ash said suddenly. "I think I know exactly what we should do." He leaned in close, whispering his plans in Misty's ear, and as her smile grew exponentially, Gary knew he was about to learn his lesson in the worst possible way.

Casey arrived a ten minutes later with her complete collection of Electabuzz musical merchandise (including a rather unfortunate musical theatre piece). It would be years before Gary successfully got the Electabuzz team song out of his head.

He should've known he was never going to win.

Not against Ash.

Not when it came to Misty.


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